WO2012029700A1 - Composition pour couche isolante d'un transistor en couches minces organique, et transistor en couches minces organique - Google Patents
Composition pour couche isolante d'un transistor en couches minces organique, et transistor en couches minces organique Download PDFInfo
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- WO2012029700A1 WO2012029700A1 PCT/JP2011/069415 JP2011069415W WO2012029700A1 WO 2012029700 A1 WO2012029700 A1 WO 2012029700A1 JP 2011069415 W JP2011069415 W JP 2011069415W WO 2012029700 A1 WO2012029700 A1 WO 2012029700A1
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- group
- film transistor
- organic thin
- insulating layer
- carbon atoms
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- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MYGFXCLXHGITIQ-UHFFFAOYSA-N quinolin-4-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=NC2=C1 MYGFXCLXHGITIQ-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- KBXGMZXLKCUSEB-UHFFFAOYSA-M sodium;[ethyl(oxidosulfinothioyl)amino]ethane Chemical compound [Na+].CCN(CC)S([O-])=S KBXGMZXLKCUSEB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- VEQHTYHLJYNSTG-UHFFFAOYSA-N tert-butyl 9-tert-butylperoxy-9-oxononanoate Chemical compound CC(C)(C)OOC(=O)CCCCCCCC(=O)OC(C)(C)C VEQHTYHLJYNSTG-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical class N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical class S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
Definitions
- the present invention relates to an organic thin film transistor insulating layer composition suitable for forming an insulating layer of an organic thin film transistor, and more particularly to an organic thin film transistor insulating layer composition suitable for forming an overcoat insulating layer.
- organic thin film transistors can be manufactured at a lower temperature than inorganic semiconductors
- plastic substrates and films can be used as the substrate, and by using such a substrate, a flexible, lightweight and hardly breakable element can be obtained.
- an element can be manufactured by application of a solution containing an organic material or film formation using a printing method, and a large number of elements can be manufactured on a large-area substrate at low cost.
- a voltage applied to a gate electrode acts on a semiconductor layer through a gate insulating layer to control the amount of drain current. Therefore, a gate insulating layer is formed between the gate electrode and the semiconductor layer.
- organic semiconductor compounds used in field effect organic thin film transistors are easily affected by the environment such as humidity and oxygen, and the transistor characteristics are likely to deteriorate over time due to humidity, oxygen and the like.
- the organic semiconductor compound is coated and protected by a gate insulating layer.
- an overcoat insulating layer or a gate insulating layer that covers an organic semiconductor layer in a field effect organic thin film transistor a composition containing a polymer compound and a solvent is used.
- an insulating layer or an insulating film of an organic thin film transistor such as the overcoat insulating layer and the gate insulating layer is referred to as an organic thin film transistor insulating layer.
- organic thin film transistor insulating layer material As a material constituting the organic thin film transistor insulating layer (hereinafter referred to as organic thin film transistor insulating layer material), for example, a copolymer containing tetrafluoroethylene has been proposed (Patent Document 1).
- an organic field effect transistor including an insulating layer formed using the organic thin film transistor insulating layer material has a problem that the absolute value of the threshold voltage when driven in the atmosphere is large.
- An object of the present invention is to provide an organic thin film transistor insulating layer composition capable of producing an organic thin film transistor having a small absolute value of a threshold voltage when driven in the atmosphere.
- this invention provides the composition for organic thin-film transistor insulating layers containing the compound (A) containing group which has cyclic ether structure, and a fluorine-containing solvent (B).
- the group having a cyclic ether structure is represented by the formula (1)
- R 1 to R 3 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the organic group may be substituted with a fluorine atom.
- R 4 to R 8 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the organic group may be substituted with a fluorine atom.
- the fluorine-containing solvent is an aromatic fluorine compound having 6 to 20 carbon atoms.
- the said composition for organic thin-film transistor insulating layers contains a fluororesin (C) further.
- the fluororesin (C) is at least one fluorine selected from the group consisting of a fluororesin (C-1) defined below and a fluororesin (C-2) defined below Resin.
- X represents a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom, a fluorine atom or a chlorine atom.
- R 9 represents an alkylene group.
- a hydrogen atom in the alkylene group may be substituted with a fluorine atom.
- R 10 to R 12 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the organic group may be substituted with a fluorine atom.
- R represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- Rf represents a fluorine atom or a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom.
- Raa represents a divalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the divalent organic group may be substituted with a fluorine atom.
- a represents an integer of 0 to 20, and m represents an integer of 1 to 5. When there are a plurality of Raa, they may be the same or different.
- R When there are a plurality of R, they may be the same or different. When there are a plurality of Rf, they may be the same or different. And a second unit that contains two or more first functional groups, and the first functional group reacts with active hydrogen by irradiation of electromagnetic waves or heat. Fluororesin, a functional group that generates functional groups
- the first functional group is at least one group selected from the group consisting of an isocyanato group blocked with a blocking agent and an isothiocyanato group blocked with a blocking agent.
- the first functional group is represented by formula (6)
- Xa represents an oxygen atom or a sulfur atom.
- R 13 and R 14 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. ] It is group represented by these.
- the first functional group has the formula (7)
- Xb represents an oxygen atom or a sulfur atom.
- R 15 , R 16 and R 17 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. ] It is group represented by these.
- the present invention also provides an organic thin film transistor having a source electrode, a drain electrode, a gate electrode, an organic semiconductor layer, and an insulating layer formed using any one of the organic thin film transistor insulating layer compositions.
- the insulating layer is an overcoat insulating layer.
- the present invention also provides a display member including the organic thin film transistor.
- the present invention also provides a display including the display member.
- An organic thin film transistor manufactured using the composition for an organic thin film transistor insulating layer of the present invention has a small threshold voltage absolute value when driven in the atmosphere.
- the compound (A) contained in the composition for an organic thin film transistor insulating layer of the present invention has a group having a cyclic ether structure.
- the cyclic ether structure refers to a structure in which carbon of a cyclic hydrocarbon is substituted with oxygen.
- the number of atoms forming the ring in the cyclic ether structure is preferably 10 or less, and more preferably 6 or less.
- the number of oxygen forming the ring in the cyclic ether structure is preferably 2 or less, and more preferably 1.
- the groups having a cyclic ether structure are subjected to addition reaction with each other by ring opening by a cationic polymerization initiator that generates cations by heating or light irradiation.
- the compound (A) is polymerized to become a polymer, and a film showing high tensile strength is formed.
- the group having a cyclic ether structure is preferably at least one selected from the group consisting of a group represented by formula (1) and a group represented by formula (2).
- the group represented by the formula (2) is particularly preferable because it provides a film having excellent solvent resistance.
- R 1 to R 8 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the organic group may be substituted with a fluorine atom.
- the monovalent organic group having 1 to 20 carbon atoms may be linear, branched or cyclic, and may be saturated or unsaturated.
- Examples of the monovalent organic group having 1 to 20 carbon atoms include a linear hydrocarbon group having 1 to 20 carbon atoms, a branched hydrocarbon group having 3 to 20 carbon atoms, and a cyclic hydrocarbon having 3 to 20 carbon atoms.
- Group, aromatic hydrocarbon group having 6 to 20 carbon atoms preferably linear hydrocarbon group having 1 to 6 carbon atoms, branched hydrocarbon group having 3 to 6 carbon atoms, or 3 to 6 carbon atoms.
- a linear hydrocarbon group having 1 to 20 carbon atoms a branched hydrocarbon group having 3 to 20 carbon atoms, and a cyclic hydrocarbon group having 3 to 20 carbon atoms
- the hydrogen atoms contained in these groups are substituted with fluorine atoms. May be.
- a hydrogen atom in the group may be substituted with an alkyl group, a halogen atom or the like.
- Examples of the monovalent organic group having 1 to 20 carbon atoms which may have a substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, and tertiary butyl.
- an alkyl group is preferable.
- Examples of the group having a cyclic ether structure include a group having an epoxy structure and a group having an oxetane structure.
- the group having an oxetane structure includes a group having a 3-ethyloxetane structure.
- the portion of the compound (A) excluding the group having a cyclic structure is a hydrogen atom or an organic group.
- the valence of the organic group is the number of groups having a cyclic ether structure contained in the compound (A).
- Examples of the organic group include a monovalent organic group having 1 to 20 carbon atoms and a divalent organic group having 1 to 20 carbon atoms.
- the compound (A) include bis (3′-glycidyloxypropyl) -1,1,3,3-tetramethyldisiloxane, 3-ethyl-3- (2′-ethylhexyloxymethyl) -oxetane, 3-ethyl-3- ⁇ [(3-ethyl-oxetane-3-yl) methoxy] methyl ⁇ oxetane.
- the fluorine-containing solvent (B) contained in the composition for an organic thin film transistor insulating layer of the present invention can fluidize the compound (A) in the composition under normal environmental conditions used when producing an organic thin film transistor. And is an organic compound having a fluorine atom, which is volatilizable.
- the organic thin film transistor insulating layer composition improves the property of spreading as a thin film. Therefore, the insulating layer can be thinly formed by a coating method or a printing method, and the flatness of the formed insulating layer surface is improved.
- the organic compound having a fluorine atom has poor affinity with an organic substance having no fluorine atom, and the organic layer function of the organic compound having the fluorine atom constituting the organic thin film transistor or the organic compound having the fluorine atom is used. Does not adversely affect the interface of the organic layer.
- the fluorine-containing solvent is preferably composed of carbon, hydrogen and fluorine and does not contain any other atom. This is because such an organic compound having a fluorine atom has particularly poor affinity with an organic substance having no fluorine atom.
- an aromatic compound having a fluorine atom is preferably used as the organic compound having a fluorine atom. This is because the aromatic compound having a fluorine atom is excellent in the property of dissolving the compound (A).
- a preferred fluorine-containing solvent is an aromatic fluorine compound having 6 to 20 carbon atoms.
- the aromatic fluorine compound having 6 to 20 carbon atoms include hexafluorobenzene, pentafluorotoluene, octafluorotoluene, and tetrafluoroanisole.
- a fluorine-containing solvent (B) you may use the solvent which added the leveling agent, surfactant, etc. as needed.
- the content of the fluorine-containing solvent (B) is preferably 10 to 3000 parts by weight, preferably 100 parts by weight of the compound (A) containing a group having a cyclic ether structure. Is 15 to 2000 parts by weight.
- the content of the fluorine-containing solvent (B) is appropriately determined in consideration of the film thickness of the organic thin film transistor insulating layer to be formed and the type and amount of the resin used in combination in the composition for the organic thin film transistor insulating layer. Can be adjusted.
- the composition for an organic thin film transistor insulating layer of the present invention may further contain a fluororesin (C).
- the fluororesin refers to an organic polymer having a structural unit containing a fluorine atom, for example, a repeating unit containing a fluorine atom.
- the formed insulating layer material contains an organic compound containing a fluorine atom
- the formed insulating layer has low polarity and enhanced water repellency.
- the fluororesin (C) has a functional group capable of bonding to atoms on the surface having high polarity such as a glass surface or a metal surface. If it does so, the adhesiveness with respect to glass, a metal, etc. will improve the insulating layer containing a fluororesin (C).
- An example of a preferred fluororesin (C) is one containing a hydroxyl group.
- X represents a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom, a fluorine atom or a chlorine atom.
- Examples of the monovalent organic group having 1 to 20 carbon atoms having a fluorine atom include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a fluorophenyl group, and a pentafluorophenyl group.
- X is a chlorine atom.
- R 9 represents an alkylene group.
- a hydrogen atom in the alkylene group may be substituted with a fluorine atom.
- the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, and an octylene group.
- R 9 is a butylene group.
- the fluororesin (C-1) that can be used in the present invention is, for example, a polymerizable monomer that is a raw material of the repeating unit represented by the formula (3) and a raw material of the repeating unit that is represented by the formula (4). It can be produced by a method in which a polymerizable monomer is copolymerized using a photopolymerization initiator or a thermal polymerization initiator.
- Examples of the polymerizable monomer that is a raw material for the repeating unit represented by the formula (3) include trifluoroethylene, 1,1,2-trifluoropropylene, and chlorotrifluoroethylene.
- Examples of the polymerizable monomer that is a raw material for the repeating unit represented by the formula (4) include 2-hydroxyethyl vinyl ether and 4-hydroxybutyl vinyl ether.
- photopolymerization initiator examples include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 4-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxy- 2-methylpropiophenone, 4,4′-bis (diethylamino) benzophenone, benzophenone, methyl (o-benzoyl) benzoate, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, -Phenyl-1,2-propanedione-2- (o-benzoyl) oxime, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin octyl ether, benzyl, benzyldimethyl
- the thermal polymerization initiator may be any radical polymerization initiator, such as 2,2′-azobisisobutyronitrile, 2,2′-azobisisovaleronitrile, 2,2 ′. -Azobis (2,4-dimethylvaleronitrile), 4,4'-azobis (4-cyanovaleric acid), 1,1'-azobis (cyclohexanecarbonitrile), 2,2'-azobis (2-methylpropane) ), Azo compounds such as 2,2′-azobis (2-methylpropionamidine) dihydrochloride, ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, acetylacetone peroxide, isobutyl peroxide Oxide, benzoyl peroxide, 2,4-dichlorobenzoyl peroxy Diacyl peroxides such as o-methylbenzoyl peroxide, lau
- the fluororesin (C-1) that can be used in the present invention is a polymerizable monomer that is a raw material of the repeating unit represented by the formula (3) and a polymerizable that is a raw material of the repeating unit represented by the formula (4).
- Other polymerizable monomers other than the monomer may be added during the polymerization.
- Examples of other polymerizable monomers include unsaturated hydrocarbons and derivatives thereof, and vinyl ether derivatives.
- the kind of the other polymerizable monomer is appropriately selected according to characteristics required for an insulating layer such as an overcoat insulating layer.
- Another preferred form of the polymerizable monomer is a monomer having no active hydrogen-containing group such as an alkyl group.
- unsaturated hydrocarbons and derivatives thereof examples include 1-butene, 1-pentene, 1-hexene, 1-octene, vinylcyclohexane, vinyl chloride, allyl alcohol and the like.
- vinyl ether derivatives include methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, cyclohexyl vinyl ether, and phenyl vinyl ether.
- butyl vinyl ether and cyclohexyl vinyl ether are preferable.
- the amount of the polymerizable monomer used as the raw material of the repeating unit represented by the formula (3) is adjusted so that the amount of fluorine introduced into the fluororesin (C-1) becomes an appropriate amount.
- fluororesin (C-1) examples include poly (trifluoroethylene-co-4-hydroxybutyl vinyl ether-co-ethyl vinyl ether), poly (trifluoroethylene-co-4-hydroxybutyl vinyl ether). -Co-butyl vinyl ether), poly (trifluoroethylene-co-4-hydroxybutyl vinyl ether-co-3-chloromethylphenyl vinyl ether), poly (trifluoroethylene-co-4-hydroxybutyl vinyl ether-co-vinyl cinnamate ) And the like.
- the fluororesin (C) contains a repeating unit represented by the formula (5), and the first functional group is 2
- the fluororesin (C-2) is a fluororesin (C-2) that is a functional group that contains two or more and the first functional group generates a second functional group that reacts with active hydrogen by the action of electromagnetic waves or heat.
- R 10 to R 12 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. .
- R represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- Rf represents a fluorine atom or a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom.
- Raa represents a divalent organic group having 1 to 20 carbon atoms.
- a hydrogen atom in the divalent organic group may be substituted with a fluorine atom.
- a represents an integer of 0 to 20, and m represents an integer of 1 to 5.
- the divalent organic group having 1 to 20 carbon atoms may be linear, branched or cyclic, and may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, a nitrogen atom, Hetero atoms such as oxygen atoms and sulfur atoms may be contained.
- a divalent linear aliphatic hydrocarbon group having 1 to 20 carbon atoms a divalent branched aliphatic hydrocarbon group having 3 to 20 carbon atoms
- a divalent cyclic aliphatic carbon group having 3 to 20 carbon atoms a divalent linear aliphatic hydrocarbon group having 1 to 20 carbon atoms
- a divalent branched aliphatic hydrocarbon group having 3 to 20 carbon atoms a divalent branched aliphatic hydrocarbon group having 3 to 20 carbon atoms
- a divalent cyclic aliphatic carbon group having 3 to 20 carbon atoms a divalent cyclic aliphatic carbon group having 3 to 20 carbon atoms.
- These groups may have a substituent.
- a divalent linear hydrocarbon group having 1 to 6 carbon atoms a divalent branched hydrocarbon group having 3 to 6 carbon atoms, a divalent cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkyl group, etc.
- a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with —O—CO— is preferable.
- Divalent linear aliphatic hydrocarbon group, divalent branched aliphatic hydrocarbon group and divalent cyclic aliphatic hydrocarbon group include methylene group, ethylene group, propylene group, butylene group, pentylene group, Examples include a hexylene group, an isopropylene group, an isobutylene group, a dimethylpropylene group, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, and a cyclohexylene group.
- Examples of the divalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent include a phenylene group, a naphthylene group, an anthrylene group, a dimethylphenylene group, a trimethylphenylene group, an ethylenephenylene group, and a diethylenephenylene group. , Triethylenephenylene group, propylenephenylene group, butylenephenylene group, methylnaphthylene group, dimethylnaphthylene group, trimethylnaphthylene group, vinylnaphthylene group, ethenylnaphthylene group, methylanthrylene group, ethylanthrylene group, etc. Is mentioned.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 10 to R 12 include the same groups as those of the monovalent organic group having 1 to 20 carbon atoms represented by R 1. .
- Examples of the monovalent organic group having 1 to 20 carbon atoms having a fluorine atom represented by Rf are the same as those of the monovalent organic group having 1 to 20 carbon atoms having a fluorine atom represented by X. Groups.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R include a linear hydrocarbon group having 1 to 20 carbon atoms, a branched hydrocarbon group having 3 to 20 carbon atoms, and 3 to 3 carbon atoms.
- 20 cyclic hydrocarbon groups, and aromatic hydrocarbon groups having 6 to 20 carbon atoms preferably linear hydrocarbon groups having 1 to 6 carbon atoms, branched hydrocarbon groups having 3 to 6 carbon atoms, A cyclic hydrocarbon group having 3 to 6 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms.
- a hydrogen atom in the group may be substituted with an alkyl group, a chlorine atom, a bromine atom, an iodine atom or the like.
- Examples of the monovalent organic group having 1 to 20 carbon atoms which may have a substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, and tertiary butyl.
- R 10 to R 12 are hydrogen atoms, Rf is a fluorine atom, a is 0, and m is 5.
- the fluororesin (C-2) that may be used in the present invention contains a repeating unit represented by the formula (5) and contains two or more first functional groups, and the first functional groups However, it contains a functional group that generates a second functional group that reacts with active hydrogen by the irradiation of electromagnetic waves or the action of heat.
- Active hydrogen refers to a hydrogen atom bonded to an atom other than a carbon atom such as an oxygen atom, a nitrogen atom and a sulfur atom.
- the second functional group that reacts with active hydrogen is preferably protected (blocked) until heat is applied in the step of forming the gate insulating layer.
- the first functional group is preferably deprotected by heat to generate a second functional group that reacts with active hydrogen. This is because the storage stability of the composition is improved.
- Examples of the first functional group include an isocyanato group blocked with a blocking agent or an isothiocyanato group blocked with a blocking agent.
- the isocyanato group blocked with the blocking agent or the blocked isothiocyanato group includes a blocking agent having only one active hydrogen capable of reacting with an isocyanato group or isothiocyanato group in one molecule of the blocking agent, an isocyanato group or isothiocyanato. It can be produced by reacting with a group.
- the blocking agent is preferably one that dissociates at a temperature of 170 ° C. or lower even after reacting with an isocyanato group or an isothiocyanato group.
- the blocking agent include alcohol compounds, phenol compounds, active methylene compounds, mercaptan compounds, acid amide compounds, acid imide compounds, imidazole compounds, urea compounds, and oxime compounds. , Amine compounds, imine compounds, bisulfites, pyridine compounds, and pyrazole compounds. These blocking agents may be used alone or in combination of two or more.
- Preferable blocking agents include oxime compounds and pyrazole compounds.
- Examples of the alcohol compounds include methanol, ethanol, propanol, butanol, 2-ethylhexanol, methyl cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, cyclohexanol and the like.
- examples of phenolic compounds include phenol, cresol, ethylphenol, butylphenol, nonylphenol, dinonylphenol, styrenated phenol, hydroxybenzoic acid ester, and the like.
- Examples of the active methylene compound include dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, and acetylacetone.
- Examples of mercaptan compounds include butyl mercaptan and dodecyl mercaptan.
- acid amide compounds include acetanilide, acetic acid amide, ⁇ -caprolactam, ⁇ -valerolactam, and ⁇ -butyrolactam
- examples of acid imide compounds include succinimide and maleic imide.
- Examples of the imidazole compound include imidazole and 2-methylimidazole.
- Examples of urea compounds include urea, thiourea, and ethylene urea.
- Examples of oxime compounds include formal oxime, acetal oxime, acetoxime, methyl ethyl ketoxime, cyclohexanone oxime, and the like.
- Examples of the amine compound include diphenylamine, aniline, carbazole and the like.
- Examples of the imine compound include ethyleneimine and polyethyleneimine.
- Examples of the bisulfite include sodium bisulfite.
- Examples of pyridine compounds include 2-hydroxypyridine and 2-hydroxyquinoline.
- Examples of the pyrazole compound include 3,5-dimethylpyrazole, 3,5-diethylpyrazole and the like.
- the isocyanato group blocked with a blocking agent that may be used in the present invention is a group represented by the formula (6), a group in which Xa is an oxygen atom, a group represented by the formula (7), A group in which Xb is an oxygen atom is preferable.
- the isothiocyanato group blocked with a blocking agent that may be used in the present invention is a group represented by the formula (6), wherein Xa is a sulfur atom, or a group represented by the formula (7). A group in which Xb is a sulfur atom is preferred.
- Xa represents an oxygen atom or a sulfur atom
- R 13 and R 14 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 13 and R 14 include the same groups as those of the monovalent organic group represented by R 10 to R 12 .
- Xa is an oxygen atom
- R 13 is a methyl group
- R 14 is an ethyl group.
- Xb represents an oxygen atom or a sulfur atom
- R 15 , R 16 and R 17 each independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 15 , R 16 and R 17 include the same groups as the examples of the monovalent organic group represented by R 10 to R 12. .
- Xb is an oxygen atom
- R 15 to R 17 are hydrogen atoms.
- Examples of the isocyanato group blocked with a blocking agent include O- (methylideneamino) carboxyamino group, O- (1-ethylideneamino) carboxyamino group, O- (1-methylethylideneamino) carboxyamino group, O— [1-methylpropylideneamino] carboxyamino group, (N-3,5-dimethylpyrazolylcarbonyl) amino group, (N-3-ethyl-5-methylpyrazolylcarbonyl) amino group, (N-3,5-diethyl) And pyrazolylcarbonyl) amino group, (N-3-propyl-5-methylpyrazolylcarbonyl) amino group, and (N-3-ethyl-5-propylpyrazolylcarbonyl) amino group.
- Examples of the isothiocyanato group blocked with a blocking agent include an O- (methylideneamino) thiocarboxyamino group, an O- (1-ethylideneamino) thiocarboxyamino group, and an O- (1-methylethylideneamino) thiocarboxyamino group.
- the first functional group used in the present invention is preferably an isocyanato group blocked with a blocking agent.
- the fluororesin (C-2) for example, comprises a polymerizable monomer that is a raw material of the repeating unit represented by the formula (5) and a polymerizable monomer containing the first functional group, a photopolymerization initiator or a heat It can manufacture by the method of copolymerizing using a polymerization initiator.
- the photopolymerization initiator and the thermal polymerization initiator include the same photopolymerization initiator and thermal polymerization initiator that can be used for the production of the fluororesin (C-1).
- Examples of the polymerizable monomer that is a raw material for the repeating unit represented by the formula (5) include 2-trifluoromethylstyrene, 3-trifluoromethylstyrene, 4-trifluoromethylstyrene, 2,3,4,5,6. -Pentafluorostyrene, 4-fluoromethylstyrene and the like.
- Examples of the polymerizable monomer containing the first functional group include an isocyanato group blocked with a blocking agent or a monomer having an isothiocyanate group blocked with a blocking agent and an unsaturated bond.
- a monomer having an isocyanato group blocked with the blocking agent or an isothiocyanate group blocked with a blocking agent and an unsaturated bond includes an isocyanate group or a compound having an isothiocyanato group and an unsaturated bond, and a blocking agent. It can be produced by reacting.
- As the unsaturated bond an unsaturated double bond is preferable.
- Examples of the compound having an unsaturated double bond and an isocyanato group include 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate, 2- (2'-methacryloyloxyethyl) oxyethyl isocyanate, and the like.
- Examples of the compound having an unsaturated double bond and an isothiocyanato group include 2-acryloyloxyethyl isothiocyanate, 2-methacryloyloxyethyl isothiocyanate, 2- (2'-methacryloyloxyethyl) oxyethyl isothiocyanate, and the like.
- the above blocking agents can be preferably used.
- an organic solvent, a catalyst, or the like may be added as necessary.
- the fluororesin (C-2) that can be used in the present invention is a polymerization monomer other than the polymerizable monomer that is a raw material of the repeating unit represented by the formula (5) and the polymerizable monomer containing the first functional group.
- a monomer capable of being added may be added during the polymerization.
- Examples of the other polymerizable monomers include acrylic acid esters and derivatives thereof, methacrylic acid esters and derivatives thereof, styrene and derivatives thereof, vinyl acetate and derivatives thereof, methacrylonitrile and derivatives thereof, acrylonitrile and derivatives thereof, organic Vinyl esters of carboxylic acids and derivatives thereof, allyl esters of organic carboxylic acids and derivatives thereof, dialkyl esters of fumaric acid and derivatives thereof, dialkyl esters of maleic acid and derivatives thereof, dialkyl esters of itaconic acid and derivatives thereof, organic carboxylic acids Examples include N-vinylamide derivatives, maleimides and derivatives thereof, terminal unsaturated hydrocarbons and derivatives thereof, and organogermanium compounds containing unsaturated bonds.
- the kind of the other polymerizable monomer is appropriately selected according to the characteristics required for the insulating layer.
- a monomer that has a high molecular density and forms a hard film such as styrene or a styrene derivative is selected.
- monomers that impart flexibility such as methacrylic acid esters and derivatives thereof, acrylic acid esters and derivatives thereof are selected.
- a monomer that does not have an active hydrogen-containing group such as an alkyl group such as a methyl group or an ethyl group is selected.
- a fluororesin polymerized by combining a polymerizable monomer as a raw material of the repeating unit represented by the formula (5) and styrene or a styrene derivative having no active hydrogen-containing group in the composition for an organic thin film transistor insulating layer by using a fluororesin polymerized by combining a polymerizable monomer as a raw material of the repeating unit represented by the formula (5) and styrene or a styrene derivative having no active hydrogen-containing group in the composition for an organic thin film transistor insulating layer.
- a gate insulating layer having high durability and low hysteresis can be obtained.
- acrylate esters and derivatives thereof monofunctional acrylates and polyfunctional acrylates with restrictions on the amount of use can be used.
- methacrylic acid esters and derivatives thereof monofunctional methacrylates and polyfunctional methacrylates can be used although there are restrictions on the amount used, for example, methyl methacrylate, methacrylic acid Ethyl, methacrylic acid-n-propyl, isopropyl methacrylate, methacrylic acid-n-butyl, isobutyl methacrylate, methacrylic acid-sec-butyl, hexyl methacrylate, octyl methacrylate, methacrylic acid 2-ethylhexyl, decyl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenyl methacrylate, benzyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, methacrylic acid -3-hydroxy Lopyl, 2-hydroxybutyl methacrylate, 2-hydroxyphenyl ethyl
- styrene and derivatives thereof include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, 2,6-dimethylstyrene, and 3,4-dimethyl.
- Styrene 3,5-dimethylstyrene, 2,4,6-trimethylstyrene, 2,4,5-trimethylstyrene, pentamethylstyrene, o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, o-chlorostyrene , M-chlorostyrene, p-chlorostyrene, o-bromostyrene, m-bromostyrene, p-bromostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-hydroxystyrene, m-hydroxystyrene , P-hydroxystyrene, 2-vinylbiphenyl, 3-biphenyl Rubiphenyl, 4-vinylbiphenyl, 1-vinylnaphthalene, 2-vin
- Acrylonitrile and its derivatives include acrylonitrile and the like.
- Examples of methacrylonitrile and derivatives thereof include methacrylonitrile.
- vinyl esters of organic carboxylic acids and derivatives thereof include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate, and divinyl adipate.
- allyl esters of organic carboxylic acids and derivatives thereof include allyl acetate, allyl benzoate, diallyl adipate, diallyl terephthalate, diallyl isophthalate, and diallyl phthalate.
- Dialkyl esters of fumaric acid and derivatives thereof include dimethyl fumarate, diethyl fumarate, diisopropyl fumarate, di-sec-butyl fumarate, diisobutyl fumarate, di-n-butyl fumarate, di-2-ethylhexyl fumarate And dibenzyl fumarate.
- Dialkyl esters of maleic acid and derivatives thereof include dimethyl maleate, diethyl maleate, diisopropyl maleate, di-sec-butyl maleate, diisobutyl maleate, di-n-butyl maleate, di-2-ethylhexyl maleate And dibenzyl maleate.
- Dialkyl esters of itaconic acid and its derivatives include dimethyl itaconate, diethyl itaconate, diisopropyl itaconate, di-sec-butyl itaconate, diisobutyl itaconate, di-n-butyl itaconate, di-2-ethylhexyl itaconate And dibenzyl itaconate.
- N-vinylamide derivatives of organic carboxylic acids examples include N-methyl-N-vinylacetamide.
- maleimide and derivatives thereof include N-phenylmaleimide and N-cyclohexylmaleimide.
- terminal unsaturated hydrocarbons and derivatives thereof examples include 1-butene, 1-pentene, 1-hexene, 1-octene, vinylcyclohexane, vinyl chloride, and allyl alcohol.
- Examples of the unsaturated bond-containing organic germanium compound include allyltrimethylgermanium, allyltriethylgermanium, allyltributylgermanium, trimethylvinylgermanium, triethylvinylgermanium, and the like.
- acrylic acid alkyl ester methacrylic acid alkyl ester, styrene, acrylonitrile, methacrylonitrile, and allyltrimethylgermanium are preferable.
- the amount of fluorine introduced into the fluororesin (C) is preferably 1 to 60% by mass, more preferably 5 to 50% by mass, and further preferably 5 to 40% by mass with respect to the mass of the polymer compound. . If the amount of fluorine is less than 1% by mass or more than 60% by mass, the compatibility with the fluorinated solvent (B) may deteriorate and it may be difficult to prepare a composition.
- the fluororesin (C) is preferably a polymer compound having a weight average molecular weight of 3000 to 1000000, more preferably 5000 to 500000.
- the fluororesin (C) may be linear, branched or cyclic.
- photo cationic polymerization initiator and the thermal cationic polymerization initiator examples include iodonium salts and sulfonium salts.
- iodonium salt examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, tolylcumyl iodonium tetrakis (pentafluorophenyl) borate, and the like.
- sulfonium salt examples include triphenylsulfonium phosphate, p- (phenylthio) phenyldiphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, p- (phenylthio) phenyldiphenylsulfonium hexafluoroantimonate, 4,4′- Bis [di ( ⁇ -hydroxyethoxy) phenylsulfonio] phenyl sulfide-bis-hexafluoroantimonate, 4- [4- (4-tert-butylbenzoyl) phenylthio] phenyl-di (4-methylphenyl) sulfonium hexafluoro A phosphate etc. are mentioned.
- photocationic polymerization initiator examples include trade name Rhodosil 2074 (manufactured by Rhodia Japan Co., Ltd.), trade name ADEKA OPTOMA-SP-150 (manufactured by ADEKA), trade name ADEKA OPTOMA-SP-152 (ADEKA Corporation).
- sulfonium salt compounds described in JP-A-9-118663 can be used.
- thermal cationic polymerization initiator examples include trade name Adeka Opton CP series (manufactured by ADEKA Corporation).
- the ratio of the photocationic polymerization initiator or the thermal cationic polymerization initiator in the composition for an organic thin film transistor insulating layer of the present invention is 100 parts by weight of the compound (A) containing a group having a cyclic ether structure.
- the range of 0.0001 to 30 parts by weight is preferable, and 0.001 to 10 parts by weight is more preferable.
- two or more kinds of the cationic photopolymerization initiator or the thermal cationic polymerization initiator may be used.
- Organic thin-film transistor insulating layer of the present invention by mixing the compound (A) containing a group having a cyclic ether structure, a fluorine-containing solvent (B), and if necessary, a fluororesin (C) and a cationic polymerization initiator The composition for use is obtained.
- the fluororesin (C) is contained in the composition for an organic thin film transistor insulating layer of the present invention, the content thereof is 600 parts by weight or less, preferably 100 to 500 parts by weight with respect to 100 parts by weight of the compound (A). is there.
- the solvent resistance of the organic thin film transistor insulating layer may be lowered.
- the content of the fluororesin (C-1) in the organic thin film transistor insulating layer composition of the present invention is A) 50 to 600 parts by weight, preferably 100 to 500 parts by weight, and more preferably 200 to 400 parts by weight with respect to 100 parts by weight.
- the coating film may be aggregated during drying. When it exceeds the weight part, the solvent resistance of the organic thin film transistor insulating layer may be lowered.
- the content of the fluorine-containing solvent (B) in the composition for an organic thin film transistor insulating layer is 100 to 3000 parts by weight, preferably 500 to 2000 parts by weight, based on 100 parts by weight of the compound (A).
- the amount is preferably 800 to 1500 parts by weight.
- the content of the fluorine-containing solvent (B) in the composition for an organic thin film transistor insulating layer is less than 100 parts by weight with respect to 100 parts by weight of the compound (A), the flatness of the coating film may be deteriorated. When it exceeds the part, the film quality of the coating film is deteriorated, and pinholes may be generated in the organic thin film transistor insulating layer.
- a fluororesin (C-1) having a hydroxyl group and a fluororesin (C-2) containing a functional group that reacts with active hydrogen may be used. Since the functional groups contained in the fluororesin (C-1) and the fluororesin (C-2) react with each other to form a crosslinked structure inside the organic thin film transistor insulating layer, polarization of the insulating layer is suppressed, and resistance Increases solvent resistance.
- the composition for an organic thin film transistor insulating layer of the present invention is a composition used for forming an insulating layer contained in an organic thin film transistor.
- a composition for organic thin-film transistor insulating layers the composition for organic thin-film transistor overcoat layers used for formation of an overcoat layer and the composition for organic thin-film transistor gate insulating layers used for formation of a gate insulating layer are mentioned.
- the organic thin film transistor insulating layer composition is preferably used for forming an overcoat layer of an organic thin film transistor.
- the overcoat layer formed using the composition for an organic thin film transistor insulating layer of the present invention is excellent in insulation and airtightness. Therefore, the organic thin film transistor having the overcoat layer can be driven stably in the atmosphere because the organic semiconductor compound contained in the transistor is effectively cut off from the surrounding environment.
- FIG. 1 is a schematic cross-sectional view showing the structure of a bottom gate top contact organic thin film transistor according to an embodiment of the present invention.
- the organic thin film transistor includes a substrate 1, a gate electrode 2 formed on the substrate 1, a gate insulating layer 3 formed on the gate electrode 2, an organic semiconductor layer 4 formed on the gate insulating layer 3, A source electrode 5 and a drain electrode 6 formed on the organic semiconductor layer 4 with a channel portion interposed therebetween, and an overcoat insulating layer 7 covering the entire element are provided.
- a bottom gate top contact type organic thin film transistor includes, for example, a gate electrode formed on a substrate, a gate insulating layer formed on the gate electrode, an organic semiconductor layer formed on the gate insulating layer, and a source electrode formed on the organic semiconductor layer. It can be manufactured by forming a drain electrode and forming an overcoat insulating layer.
- FIG. 2 is a schematic cross-sectional view showing the structure of a bottom gate bottom contact type organic thin film transistor which is an embodiment of the present invention.
- a substrate 1 a gate electrode 2 formed on the substrate 1, a gate insulating layer 3 formed on the gate electrode 2, and a channel portion on the gate insulating layer 3 are formed.
- a source electrode 5 and a drain electrode 6, an organic semiconductor layer 4 formed on the source electrode 5 and the drain electrode 6, and an overcoat insulating layer 7 covering the entire element are provided.
- a bottom gate bottom contact type organic thin film transistor includes, for example, a gate electrode formed on a substrate, a gate insulating layer formed on the gate electrode, a source electrode and a drain electrode formed on the gate insulating layer, and a source electrode and a drain electrode. It can be manufactured by forming an organic semiconductor layer thereon and forming an overcoat insulating layer.
- the overcoat insulating layer is formed by applying, drying and curing the overcoat insulating layer composition of the present invention on the organic semiconductor layer.
- the overcoat insulating layer composition can be applied onto the organic semiconductor layer by known spin coating, die coating, screen printing, ink jetting or the like.
- the substrate 1, the gate electrode 2, the source electrode 5, the drain electrode 6, and the organic semiconductor layer 4 that constitute the organic thin film transistor may be formed of materials and methods that are usually used.
- a resin or plastic plate or film, a glass plate, a silicon plate, or the like is used as the substrate material.
- the material of the electrode chromium, gold, silver, aluminum or the like is used, and it is formed by a known method such as a vapor deposition method, a sputtering method, a printing method, or an ink jet method.
- organic semiconductor compounds As organic semiconductor compounds, ⁇ -conjugated polymers are widely used. For example, polypyrroles, polythiophenes, polyanilines, polyallylamines, fluorenes, polycarbazoles, polyindoles, poly (p-phenylene vinylene) s are used. Can do. In addition, low-molecular substances having solubility in organic solvents, for example, polycyclic aromatic derivatives such as pentacene, phthalocyanine derivatives, perylene derivatives, tetrathiafulvalene derivatives, tetracyanoquinodimethane derivatives, fullerenes, carbon nanotubes Can be used. Specific examples include condensates of 9,9-di-n-octylfluorene-2,7-di (ethylene boronate) and 5,5′-dibromo-2,2′-bithiophene. .
- the formation of the organic semiconductor layer is performed, for example, by adding a solvent or the like to the organic semiconductor compound to prepare an organic semiconductor coating solution, and applying and drying this on the gate insulating layer.
- the solvent to be used is not particularly limited as long as it dissolves or disperses the organic semiconductor compound, but a solvent having a boiling point of 50 ° C. to 200 ° C. at normal pressure is preferable.
- the solvent include chloroform, toluene, anisole, 2-heptanone, propylene glycol monomethyl ether acetate and the like.
- the organic semiconductor coating solution can be applied onto the gate insulating layer by known spin coating, die coating, screen printing, ink jetting, or the like in the same manner as the insulating layer coating solution.
- a display member having an organic thin film transistor can be suitably produced using the organic thin film transistor of the present invention.
- a display including the display member can be suitably produced.
- Synthesis example 1 (Synthesis of polymer compound 1) Under an inert atmosphere, 5.7 g of 2,7-bis (1,3,2-dioxaborolan-2-yl) -9,9-dioctylfluorene, bis (4-bromophenyl)-(4-secondarybutylphenyl) -4.50 g of amine, 2.2 mg of palladium acetate, 15.1 mg of tri (2-methylphenyl) phosphine, methyltrioctylammonium chloride (manufactured by Aldrich, trade name “Aliquat® 336”) 91 g and 70 ml of toluene were mixed and heated to 105 ° C.
- the obtained toluene solution was dropped into methanol (3 L) and stirred for 3 hours, and then the obtained solid was collected by filtration and dried.
- the yield of the obtained polymer compound 1 represented by the following formula was 5.25 g.
- n in the following formula represents the degree of polymerization.
- required from the standard polystyrene of the high molecular compound 1 was 2.6 * 10 ⁇ 5 >.
- the measurement conditions of the weight average molecular weight were apparatus: GPC manufactured by Shimadzu, column: one “Tskel super HM-H” + one “Tskel super H2000”, and mobile phase: THF.
- Synthesis example 2 (Synthesis of polymer compound 2) 2,3,4,5,6-pentafluorostyrene (Aldrich) 2.00 g, 2,2′-azobis (2-methylpropionitrile) 0.01 g, 2,3,4,5,6-penta Put 3.00 g of fluorotoluene (manufactured by Wako Pure Chemical Industries, Ltd.) into a 50 ml pressure vessel (manufactured by Ace), bubble with argon, seal tightly, and polymerize in an oil bath at 60 ° C. for 24 hours. Thus, a 2,3,4,5,6-pentafluorotoluene solution of polymer compound 2 was obtained.
- n in the following formula represents the degree of polymerization.
- the weight average molecular weight obtained from the standard polystyrene of the obtained polymer compound 2 was 88,000.
- the conditions for measuring the weight average molecular weight were the same as those described in Synthesis Example 1.
- Example 1 (Preparation of Composition 1 for Organic Thin Film Transistor Insulating Layer)
- the obtained solution was filtered through a membrane filter having a pore diameter of 0.45 ⁇ m to prepare an organic thin film
- Alignin oxetane (registered trademark) OXT-221 is a compound having a structure represented by the following formula.
- “Lumiflon (registered trademark) LF200F” is a polymer compound having a repeating unit represented by the formula (2-a) and a repeating unit represented by the formula (3-a).
- X represents a fluorine atom, a chlorine atom or a trifluoromethyl group.
- R 4 represents an alkylene group.
- Polymer compound 1 was dissolved in xylene to prepare a solution (organic semiconductor composition) having a concentration of 0.5% by weight, and the solution was filtered through a membrane filter having a pore size of 0.45 ⁇ m to prepare a coating solution. .
- the obtained coating solution containing the polymer compound 1 is applied on a bottom gate bottom contact element (manufactured by Kyodo Inter) by a spin coating method and dried in nitrogen at 200 ° C. for 10 minutes to obtain an active layer having a thickness of about 60 nm. Formed. Subsequently, the composition 1 for organic thin-film transistor insulating layers was apply
- a UV / ozone cleaner Model UV-1, manufactured by Samco
- Comparative Example 1 (Production of field-effect organic thin-film transistors) Instead of the composition 1 for an organic thin film transistor insulating layer, 1 part of 2,3,4,5,6-pentafluorotoluene is added to 1.00 g of a 2,3,4,5,6-pentafluorotoluene solution of the polymer compound 2.
- a field effect organic thin film transistor was produced in the same manner as in Example 1 except that 0.000 g was added and the composition 2 for an organic thin film transistor insulating layer prepared by filtering through a membrane filter having a pore diameter of 0.45 ⁇ m was used. The transistor characteristics were measured. The thickness of the overcoat insulating layer was about 6 ⁇ m.
- the absolute value of the threshold voltage was 40 V or more, and the device was not driven under the conditions where the gate voltage Vg was changed to 20 to ⁇ 40 V and the source-drain voltage Vsd was changed to 0 to ⁇ 40 V.
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Abstract
[Problème] L'invention concerne une composition pour la couche isolante d'un transistor en couches minces organique qui permet de fabriquer un transistor en couches minces organique avec une tension de seuil de faible valeur absolue quand le transistor fonctionne dans des conditions atmosphériques. [Solution] Ladite composition comprend (A) un composé contenant un groupe ayant une structure d'éther cyclique dans ses molécules, et (B) un solvant contenant du fluor.
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JP6056443B2 (ja) * | 2012-12-12 | 2017-01-11 | 住友化学株式会社 | 絶縁層材料及び該絶縁層材料を用いて形成した有機薄膜トランジスタ |
WO2015098192A1 (fr) * | 2013-12-27 | 2015-07-02 | シャープ株式会社 | Dispositif à semi-conducteurs et dispositif d'affichage |
JP6624080B2 (ja) | 2015-02-05 | 2019-12-25 | Agc株式会社 | 感光性樹脂組成物、樹脂膜の製造方法および有機半導体素子の製造方法 |
JP6443148B2 (ja) * | 2015-03-16 | 2018-12-26 | 住友化学株式会社 | 組成物および該組成物を用いて製造される膜 |
WO2016152090A1 (fr) * | 2015-03-25 | 2016-09-29 | 凸版印刷株式会社 | Transistor à couches minces, procédé de fabrication de transistor à couches minces, et dispositif d'affichage d'image utilisant un transistor à couches minces |
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- 2011-08-29 WO PCT/JP2011/069415 patent/WO2012029700A1/fr active Application Filing
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JP5890633B2 (ja) | 2016-03-22 |
TWI488845B (zh) | 2015-06-21 |
JP2012074683A (ja) | 2012-04-12 |
TW201219376A (en) | 2012-05-16 |
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